1. Field of the Invention
This invention concerns novel oxime ether derivatives of certain bicyclo[3.2.0.]heptan-6-ones and pharmaceutically acceptable salts and esters thereof, their use in treating cardiovascular disorders, pharmaceutical compositions containing these compounds, and methods of preparing such compounds.
2. Related Disclosures
Bicyclo[3.2.0]hept-2-en-6-one is readily prepared from cyclopentadiene. (J. Org. Chem., 37: 2363, 1972). This and related cycloheptanones are key intermediates in various prostaglandin syntheses. Bindra and Bindra, Prostaglandin Synthesis, Acad. Press, N.Y. (1977). They are also known to be used in the manufacture of fragrant compounds (Belgium Pat. No. BE-862-775 to Allen and Hanburys, Ltd.; and Russian Pat. No. SU-639-854 to Zelinskii of Org. Chem. Institute, USSR).
Synthetic prostaglandin analogues with a bicyclo [2.2.1]heptane skeleton which incorporate an oxime ether moiety in the .omega.-side chain are described in U.S. Pat. No. 3,872,169 to Bellina of E.I. du Pont de Nemours.
Oxyimino-substituted (lR,cis)-cyclopropanecarboxylate and oxyimino-substituted (lR,trans)-cyclopropanecarboxylates are useful as pesticides (U.S. Pat. Nos. 4,211,789 and 4,211,792 to Roman et al of Shell Oil Company, and 4,219,563 to Powel of Shell Oil Company).
Compounds structurally related to those of the present invention are bicyclo[2.2.1]heptanes or heptanones which are substituted at the 5-position by a 6-carboxy-hex-2-enyl group and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic or aromatic hydrocarbon residue or aliphatic hydrocarbon residue substituted directly or through an oxygen or sulfur atom by an aromatic residue. (PCT International Application No. PCT/GB80/00001, PCT International Publication No. WO 80/01381).